Not to be confused with
hyoscine , another name for the drug scopolamine.
Tropane alkaloid
Pharmaceutical compound
Hyoscyamine Clinical data Trade names Anaspaz, Levbid, Levsin AHFS /Drugs.com Monograph MedlinePlus a684010 Routes of By mouth , InjectionATC code Legal status Legal status Pharmacokinetic dataBioavailability 50% protein binding Metabolism Liver Eliminationhalf-life 3–5 hrs. Excretion Kidney Identifiers CAS Number PubChem CID DrugBank ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA) ECHA InfoCard 100.002.667 Chemical and physical data Formula C 17 H 23 N O 3 Molar mass −1 3D model (JSmol ) InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1
Y Key:RKUNBYITZUJHSG-FXUDXRNXSA-N
Y N Y (what is this?) (verify)
Hyoscyamine (also known asdaturine orduboisine ) is a naturally occurringtropane alkaloid and plant toxin. It is asecondary metabolite found in certain plants of the familySolanaceae , includinghenbane ,mandrake ,angel's trumpets ,jimsonweed ,the sorcerers' tree , andAtropa belladonna (deadly nightshade). It is thelevorotary isomer ofatropine (third of the three major nightshade alkaloids) and thus sometimes known as levo-atropine.[ 1] [better source needed
In 2021, it was the 272nd most commonly prescribed medication in the United States, with more than 900,000 prescriptions.[ 2] [ 3]
Brand names for hyoscyamine include Symax, HyoMax, Anaspaz, Egazil, Buwecon, Cystospaz, Levsin, Levbid, Levsinex, Donnamar, NuLev, Spacol T/S, and Neoquess.[ 4]
Hyoscyamine is used to provide symptomatic relief of spasms caused by various lower abdominal and bladder disorders includingpeptic ulcers ,irritable bowel syndrome ,diverticulitis ,pancreatitis ,colic , andinterstitial cystitis .[ 5] [ 6] [ 7] Parkinson's disease , as well as for control of abnormal respiratory symptoms and "hyper-mucus secretions" in patients with lung disease.[ 8]
It is also useful in pain control for neuropathic pain, chronic pain and palliative care — "comfort care" — for those with intractable pain from treatment resistant, untreatable, and incurable diseases. When combined with opioids it increases the level of analgesia (pain relief) obtained.[ 9] hyoscine and other members of the anticholinergic drug group likecyclobenzaprine ,trihexyphenidyl , andorphenadrine are also used for this purpose.[ 10] ileus .[ 11]
Side effects include dry mouth and throat, increased appetite leading to weight gain, eye pain, blurred vision, restlessness, dizziness,arrhythmia , flushing, and faintness.[ 6] hyoscine , as well asdicycloverine ,orphenadrine ,cyclobenzaprine ,trihexyphenidyl , and ethanolamine antihistamines likephenyltoloxamine .[ 12] [ 13]
Hyoscyamine is anantimuscarinic ; i.e., an antagonist ofmuscarinic acetylcholine receptors . It blocks the action ofacetylcholine at sweat glands (sympathetic) and atparasympathetic sites in salivary glands, stomach secretions, heart muscle,sinoatrial node , smooth muscle in thegastrointestinal tract , and thecentral nervous system . It increases cardiac output and heart rate, lowers blood pressure and dries secretions.[ 14] serotonin .[ 15] [better source needed At comparable doses, hyoscyamine has 98 percent of theanticholinergic power of atropine; the other majorAtropa belladonna -derived drughyoscine (known in the United States as scopolamine) has 92 per cent of the antimuscarinic potency of atropine.[ 15] [better source needed
Hyoscyamine has been described as aselective muscarinic acetylcholineM2 receptor antagonist without significant effects at the other muscarinic acetylcholine receptors.[ 16] [ 17] atropine andscopolamine , which arenon-selective antagonists of all five muscarinic acetylcholine receptors.[ 16] [ 17] M1 receptor and M2 receptor has been implicated as having negative effects onmemory andcognition .[ 17] deliriant effects similarly to scopolamine, atropine, and other antimuscarinics.[ 16] [ 18]
Biosynthesis in plants [ edit ] Biochemistry of tropane class compounds. Hyoscyamine andscopolamine are present and labeled in the diagram. Hyoscyamine can be extracted from plants of the familySolanaceae , notablyDatura stramonium precursor in theplant biosynthesis of hyoscine , it is produced via the samemetabolic pathway .[ 19]
A generic presentation of the steps in thebiosynthesis of hyoscine, adapted from the review of Ziegler and Facchini, is illustrated below.[ 19] decarboxylation ofL -ornithine toputrescine byornithine decarboxylase (EC 4.1.1.17 ). Putrescine ismethylated toN -methylputrescine byputrescineN -methyltransferase (EC 2.1.1.53 ).[ 19]
Aputrescine oxidase (EC 1.4.3.10 ) that specifically recognizes methylated putrescine catalyzes thedeamination of this compound to 4-methylaminobutanal which then undergoes a spontaneous ring formation toN -methylpyrrolium cation. In the next step, the pyrrolium cation condenses withacetoacetic acid yieldinghygrine . No enzymatic activity could be demonstrated that catalyzes this reaction. Hygrine further rearranges totropinone .[ 19]
Subsequently,tropinone reductase I (EC 1.1.1.206 ) converts tropinone totropine which condenses withphenylalanine -derived phenyllactate to littorine.[citation needed Acytochrome P450 classified as Cyp80F1 oxidizes and rearranges littorine to hyoscyaminealdehyde .[ 20]
A plant extract used "for catching fish, in ceremony to connect with the spiritual realm", and as abush medicine , "in a sleeping potion and for a variety of other uses", was developed byAboriginal peoples from the softcorkwood tree,Duboisia myoporoides New South Wales ] across to NorthernQueensland ,Australia "; modern studies have shown the Aboriginal medicine to contain thealkaloids hyoscyamine andscopolamine .[ 21]
Ingredients of a "Clap Mixture" (medical formulation) , putatively hyoscyamine-containing,[ 22] sexually transmitted infection ,gonorrhea ".[ 23] natural product extracted from an unspecified plant. Other indicated ingredients are interpreted to be: "Sod. Cit.",sodium citrate ; "Sod. Bic.,sodium bicarbonate ; "Chlorof.",chloroform ; "Aq.",aqueous , hence, the deduction is that this is an extract ofhyoscyamine formulated for treatment of "the clap," also containingsodium citrate andsodium bicarbonate , in a solution/mixture ofchloroform and water.[citation needed [dubious discuss Society and culture [ edit ] German-Australian botanistBaron Sir Ferdinand Jacob Heinrich von Mueller , on finding thatAboriginal communities had used a softcorkwood tree (Duboisia myoporoides natural product isolate from Australia, and to create a "mystery pill" that was used by theAllies in World War II, specifically, to preventseasickness among soldiers ferried across theEnglish Channel during theInvasion of Normandy .[ 21] natural product isolate, hyoscyamine andscopolamine , could be used in pharmaceutical production—which, by virtue of use ineye surgery , led to the growth of a multi-million dollar industry inQueensland .[ 21]
A separate historic, apparent, but unsubstantiatedoff-label use of hysoscyamine was in the treatment ofsexually transmitted infections .[citation needed [dubious discuss
^ Ushimaru R, Ruszczycky MW, Liu HW (January 2019)."Changes in Regioselectivity of H Atom Abstraction during the Hydroxylation and Cyclization Reactions Catalyzed by Hyoscyamine 6β-Hydroxylase" .Journal of the American Chemical Society .141 (2):1062– 1066.Bibcode :2019JAChS.141.1062U .doi :10.1021/jacs.8b11585 .PMC 6488026 PMID 30545219 . [non-primary source needed ^ "The Top 300 of 2021" .ClinCalc .Archived from the original on 15 January 2024. Retrieved14 January 2024 .^ "Hyoscyamine - Drug Usage Statistics" .ClinCalc . Retrieved14 January 2024 .^ "Hyoscyamine - brand name list from Drugs.com" .Drugs.com Archived from the original on 20 August 2022. Retrieved20 August 2022 .^ National Clinical Guideline Centre (UK) (2012).Treatment to improve bladder storage Royal College of Physicians . p. 83 – viaNational Library of Medicine . ^a b "Hyoscyamine Uses, Side Effects & Warnings" .Drugs.com Archived from the original on 20 August 2022. Retrieved20 August 2022 .^ "Bladder Control Medicines | NIDDK" .National Institute of Diabetes and Digestive and Kidney Diseases the original on 20 August 2022. Retrieved20 August 2022 .^ "Hyoscyamine: MedlinePlus Drug Information" .medlineplus.gov Archived from the original on 20 August 2022. Retrieved20 August 2022 .^ Harden RN (March 2005). "Chronic neuropathic pain. Mechanisms, diagnosis, and treatment".The Neurologist .11 (2):111– 122.doi :10.1097/01.nrl.0000155180.60057.8e .PMID 15733333 .S2CID 12602416 . ^ Ali-Melkkilä T, Kanto J, Iisalo E (October 1993). "Pharmacokinetics and related pharmacodynamics of anticholinergic drugs".Acta Anaesthesiologica Scandinavica .37 (7):633– 642.doi :10.1111/j.1399-6576.1993.tb03780.x .PMID 8249551 .S2CID 22808654 . ^ Kamimura A, Howard S, Weaver S, Panahi S, Ashby J (December 2020)."The Use of Complementary and Alternative Medicine Strategies, Opioids, and Nonsteroidal Anti-Inflammatory Drugs (NSAIDS) Among Patients Attending a Free Clinic" .Journal of Patient Experience .7 (6):1701– 1707.doi :10.1177/2374373520937514 .PMC 7786764 PMID 33457633 . ^ Kang M, Galuska MA, Ghassemzadeh S (2022)."Benzodiazepine Toxicity" .StatPearls . Treasure Island (FL): StatPearls Publishing.PMID 29489152 .Archived from the original on 20 August 2022. ^ "Hyoscyamine Sulfate Sublingual Tablets, 0.125 mgRx Only" .www.dailymed.nlm.nih.gov .Archived from the original on 20 August 2022. Retrieved20 August 2022 .^ Edwards Pharmaceuticals, Inc., Belcher Pharmaceuticals, Inc. (May 2010)."DailyMed" . U.S. National Library of Medicine. Retrieved13 January 2013 . ^a b Kapoor AK, Raju SM (2013). "2.3 Cholinergic Drugs—Antagonists (Inhibition) of Cholinergic Receptors".Illustrated Medical Pharmacology 129– 131, esp. 131.ISBN 9789350906552 . Retrieved11 January 2014 . [better source needed Note, no actual content is available via the current web link.^a b c Lakstygal AM, Kolesnikova TO, Khatsko SL, Zabegalov KN, Volgin AD, Demin KA, et al. (May 2019)."DARK Classics in Chemical Neuroscience: Atropine, Scopolamine, and Other Anticholinergic Deliriant Hallucinogens" (review) .ACS Chem Neurosci .10 (5):2144– 2159.doi :10.1021/acschemneuro.8b00615 .PMID 30566832 . Retrieved12 August 2025 . ^a b c Shim KH, Kang MJ, Sharma N, An SS (September 2022)."Beauty of the Beast: Anticholinergic Tropane Alkaloids in Therapeutics" .Nat Prod Bioprospect .12 (1) 33.doi :10.1007/s13659-022-00357-w .PMC 9478010 PMID 36109439 .Antagonism at M1 and M2 receptors have negative impact on memory and cognition... Atropine and scopolamine are non-selective competitive antagonist of muscarinic receptors. Atropine has the highest affinity for subtype M1, followed by M2 and M3 and weak affinity for M4 and M5... On the other hand, scopolamine has strong affinity for M1-M4 compared to M5... while hyoscyamine binds to M2 only... ^ Lavrador M, Cabral AC, Veríssimo MT, Fernandez-Llimos F, Figueiredo IV, Castel-Branco MM (January 2023)."A Universal Pharmacological-Based List of Drugs with Anticholinergic Activity" .Pharmaceutics .15 (1): 230.doi :10.3390/pharmaceutics15010230 PMC 9863833 PMID 36678858 . ^a b c d Ziegler J, Facchini PJ (2008)."Alkaloid biosynthesis: metabolism and trafficking" Annual Review of Plant Biology .59 (1):735– 769.Bibcode :2008AnRPB..59..735Z .doi :10.1146/annurev.arplant.59.032607.092730 .PMID 18251710 . ^ Li R, Reed DW, Liu E, Nowak J, Pelcher LE, Page JE, et al. (May 2006)."Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement" .Chemistry & Biology .13 (5):513– 520.doi :10.1016/j.chembiol.2006.03.005 PMID 16720272 . ^a b c KCL Staff & Healy, Jacky (7 June 2019)."Visitors to Art of Healing Exhibition Told How Australian Indigenous Bush Medicine Was Given to Every Allied Soldier Landing at Normandy on D-Day" .KCL.ac.uk . London, England: Bush House, King's College London (KCL). Retrieved12 August 2025 . ^ Benn Brothers (1929).Chemist and Druggist: The Newsweekly for Pharmacy, Vol. 111 ^ Merriam-Webster. (n.d.)."The Clap. In Merriam-Webster.com dictionary" . Retrieved12 August 2025 . https://www.merriam-webster.com/dictionary/the%20clap .
Plants / animals Preparations Compounds People
Psychedelics (5-HT2A R agonists) Tryptamines (e.g.,DMT ,psilocin ,psilocybin ,bufotenin ,5-MeO-DMT ,AMT )Phenethylamines (e.g.,mescaline ,2C-B ,DOM ,MDA ,TMA ,2C-B-FLY ,25I-NBOMe )Lysergamides (e.g.,LSD ,ergine ,isoergine )Others (e.g.,quipazine ,efavirenz ) For a full list of serotonergic psychedelics, see the navboxhere and the listhere instead. Dissociatives (NMDAR antagonists )
Deliriants (mAChR antagonists ) Cannabinoids (CB1 R agonists)
κOR agonists GABAA R agonists Inhalants (mixedMoA Tooltip mechanism of action )Others Aminochromes (e.g.,adrenochrome ,adrenolutin )Carbogen CertainGABAA receptor positive allosteric modulators (nonbenzodiazepines /Z-drugs ) (e.g.,eszopiclone ,zaleplon ,zolpidem ,zopiclone ) CI-966 Cryogenine Glaucine Hallucinogenic bolete mushrooms (e.g.,Lanmaoa asiatica Harmala alkaloidsβ-carbolines (e.g.,harmaline ,6-methoxyharmalan )Iboga alkaloidsazepinoindoles (e.g.,ibogaine )Isoaminile Noscapine Nutmeg (e.g.,myristicin ,elemicin )Oneirogens (e.g.,Calea zacatechichi galantamine ,nicotine ,Silene capensis Prenoxdiazine Pukateine
mAChRs Tooltip Muscarinic acetylcholine receptors
Agonists Antagonists 3-Quinuclidinyl benzilate 4-DAMP Aclidinium bromide (+formoterol )Abediterol AF-DX 250 AF-DX 384 Ambutonium bromide Anisodamine Anisodine Antihistamines (first-generation) (e.g.,brompheniramine ,buclizine ,captodiame ,chlorphenamine (chlorpheniramine) ,cinnarizine ,clemastine ,cyproheptadine ,dimenhydrinate ,dimetindene ,diphenhydramine ,doxylamine ,meclizine ,mequitazine ,perlapine ,phenindamine ,pheniramine ,phenyltoloxamine ,promethazine ,propiomazine ,triprolidine )AQ-RA 741 Atropine Atropine methonitrate Atypical antipsychotics (e.g.,clozapine ,fluperlapine ,olanzapine (+fluoxetine ),rilapine ,quetiapine ,tenilapine ,zotepine )Benactyzine Benzatropine (benztropine) Benzilone Benzilylcholine mustard Benzydamine Bevonium BIBN 99 Biperiden Bornaprine Camylofin CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 Caramiphen Cimetropium bromide Clidinium bromide Cloperastine CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin DAU-5884 Desfesoterodine Dexetimide DIBD Dicycloverine (dicyclomine) Dihexyverine Difemerine Diphemanil metilsulfate Ditran Drofenine EA-3167 EA-3443 EA-3580 EA-3834 Emepronium bromide Etanautine Etybenzatropine (ethybenztropine) Fenpiverinium Fentonium bromide Fesoterodine Flavoxate Glycopyrronium bromide (+beclometasone/formoterol ,+indacaterol ,+neostigmine )Hexahydrodifenidol Hexahydrosiladifenidol Hexbutinol Hexocyclium Himbacine HL-031,120 Homatropine Imidafenacin Ipratropium bromide (+salbutamol )Isopropamide J-104,129 Hyoscyamine Mamba toxin 3 Mamba toxin 7 Mazaticol Mebeverine Meladrazine Mepenzolate Methantheline Methoctramine Methylatropine Methylhomatropine Methylscopolamine Metixene Muscarinic toxin 7 N-Ethyl-3-piperidyl benzilate N-Methyl-3-piperidyl benzilate Nefopam Octatropine methylbromide (anisotropine methylbromide) Orphenadrine Otenzepad (AF-DX 116) Otilonium bromide Oxapium iodide Oxitropium bromide Oxybutynin Oxyphencyclimine Oxyphenonium bromide PBID PD-102,807 PD-0298029 Penthienate Pethidine pFHHSiD Phenglutarimide Phenyltoloxamine Pipenzolate bromide Piperidolate Pirenzepine Piroheptine Pizotifen Poldine Pridinol Prifinium bromide Procyclidine Profenamine (ethopropazine) Propantheline bromide Propiverine Quinidine 3-Quinuclidinyl thiochromane-4-carboxylate Revefenacin Rociverine RU-47,213 SCH-57,790 SCH-72,788 SCH-217,443 Scopolamine (hyoscine) Scopolamine butylbromide (hyoscine butylbromide) Silahexacyclium Sofpironium bromide Solifenacin SSRIs Tooltip Selective serotonin reuptake inhibitors (e.g.,femoxetine ,paroxetine )Telenzepine Terodiline Tetracyclic antidepressants (e.g.,amoxapine ,maprotiline ,mianserin ,mirtazapine )Tiemonium iodide Timepidium bromide Tiotropium bromide Tiquizium bromide Tofenacin Tolterodine Tricyclic antidepressants (e.g.,amitriptyline (+perphenazine ),amitriptylinoxide ,butriptyline ,cidoxepin ,clomipramine ,desipramine ,desmethyldesipramine ,dibenzepin ,dosulepin (dothiepin) ,doxepin ,imipramine ,lofepramine ,nitroxazepine ,northiaden (desmethyldosulepin) ,nortriptyline ,protriptyline ,quinupramine ,trimipramine )Tridihexethyl Trihexyphenidyl Trimebutine Tripitamine (tripitramine) Tropacine Tropatepine Tropicamide Tropine benzilate Trospium chloride Typical antipsychotics (e.g.,chlorpromazine ,chlorprothixene ,cyamemazine (cyamepromazine) ,loxapine ,mesoridazine ,thioridazine )Umeclidinium bromide (+vilanterol )WIN-2299 Xanomeline Zamifenacin
Precursors (andprodrugs )
N
Y (what is this?) (verify)
